


Singled out

by maekami (squorsh)



Category: Superjail!
Genre: Clothed Sex, Creampie, Fingering, Lap Sex, Other, Trans Warden, extremely flustered extremely bottom warden, he's a blushy bottom, reader has a weenie, soft sex?
Language: English
Status: Completed
Published: 2018-07-29
Updated: 2018-07-29
Packaged: 2019-06-17 22:14:01
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,604
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15471249
Author URL: https://archiveofourown.org/users/squorsh/pseuds/maekami
Summary: You are a prisoner at Superjail who somehow avoids a riot unscathed, which catches the eye of the Warden in more ways than one.





	Singled out

Superjail had been far from normal ever since you had arrived there weeks prior – with the bizarre landscapes, mass destruction, and absolute chaos that happened on a near-daily basis, you were almost used to it at this point. Regardless, being the only one left standing in the middle of the eastern courtyard spattered in blood was a new situation for you, and one that you weren’t a fan of, at that.

You weren’t sure how it all had happened, initially. One prisoner had called another one some sort of name, a fight broke out, and somehow weapons shortly became involved. The next thing you knew, the earth was covered in blood, the stench prominent in the air around you. Corpses were littered hither and yon, some only laying limply while others looked worse for the wear, mutilated and missing limbs, even. How did simple criminals have the strength to rip off body parts? Was the lunacy of Superjail somehow a part of it? You found that it hurt your head to think on it too much.

Your daze was disrupted by the sound of a mechanical hum, and you forced yourself to look upward at the source of it. The sight caused you to jolt and instinctively take a step backwards in fear, but because you had forgotten that being covered in blood and witnessing no less than twenty murders before your very eyes would more than likely shake you, your legs gave out and you fell back onto the dirt on your rear. Something was pressing against your lower back, and even you weren’t optimistic enough to think it could be anything but a corpse, or that the liquid seeping into your jumpsuit could be anything but blood.

There it was – the robot that, while you had not had any spats with personally, still filled you with fear and adrenaline. It was the thing that had plucked you from the prison bus and carried you to this hellscape, and it was the thing that you always saw mercilessly killing prisoners and making them suffer without any emotion. Its face looked obliviously happy as it floated down to ground level in the form of some sort of hovering cart, and as it made contact, you shirked back, then immediately winced upon remembering that a corpse lay behind you. 

The robot held two people: the owner of the prison that you had only seen in person on a handful of occasions in crowds, and his assistant, who was a rather short and stout little man carrying a clipboard. Both stepped out onto the dirt, the former purposefully sidestepping a splatter of blood and causing his assistant to stumble on his way out. You felt yourself wince as he lost his balance and fell back into a puddle of the liquid, looking beyond aghast, but the Warden seemed unperturbed. 

He held a hand to his forehead, surveying the area and squinting behind his yellow-tinted glasses. You wondered why he even wore those, or for that matter, why he wore any of his unusual getup, but at this point, you found it as just another part of Superjail’s strangeness that you would have to grow accustomed to. 

Lowering his gloved hand, he rested it atop the golden ball atop of the sleek black cane he held, drumming his fingers along it. “This won’t do,” he mused. “This just won’t do at all. Jared,” He faced his assistant, whom was shakily trying to get to his feet, posture stiff, “I thought I told you to make sure none of the prisoners had weapons while they were out here! This courtyard is for recreation, not… well, murder!” 

The assistant began to stammer away, occasionally gesturing to his clipboard and motioning with his free hand, sweat beading on his brow and obviously trying to ignore the dampness of the back of his suit. As they were preoccupied, you thought, foolishly, that perhaps you could move away, but you had scarcely gotten on one knee to stand up when something appeared in front of you. It was a boot attached to a purple pant leg. To your utmost confusion, it was stretched all the way over to where the Warden stood, but he shot forward towards you to stand fully, causing you to yelp and fall back down, now sprawled on top of the corpse beneath you and good lord you hoped that what was jabbing into your elbow wasn’t its fractured skull.

The man was peering down at you with squinted eyes, leaning over until his spine should have been broken, nearly face to face. He spoke, voice quiet, yet affirmative, “Are _you_ the one that did all of this?”

“No!” you immediately yelped, voice cracked and hoarse. Your hands moved upward in a surrendering position, a nervous, shaking laugh passing your lips. “I swear to god I didn’t do any of th-this; a fight just broke out, and I somehow didn’t die…”

The Warden hummed, holding a finger to his chin and peering down at you, tilting his head. You suddenly, for some reason, felt self-conscious of your appearance – covered in blood and gore, stinking of iron, your hair was a mess, and the orange jumpsuit didn’t exactly flatter one’s figure. His gaze, however, was ever-present and analytical, and finally, he straightened his posture and walked back over to his robot and assistant. They exchanged talk in hushed tones, Warden occasionally looking over to you and causing you to flinch with every glance.

Tapping his cane against the ground once, a rainbow appeared from its base and flew off into the distance, and you could only stare slackjawed as he walked off across it as if this were a completely normal occurrence. Maybe you _had_ died in the rampage, and this was purgatory. Or had Superjail been purgatory to begin with? If so, it wouldn’t exactly shock you. Did purgatory have rainbows?

You had little time to ponder such inane thoughts before the sight of the robot caught your eye, and it was advancing. A yelp escaped you, trying to scramble back to no avail, and to your horror, it extended a clawed hand and moved it over to you. Whereas you had prepared yourself for death, it only hoisted you up unceremoniously and started to fly upwards. 

Being carried over the jail by only a robotic claw was beyond terrifying, and your stomach dropped every time you looked down (which was impossible to avoid, seeing as how the bot had hoisted you up by your waist). Buildings and prisoners and drones moves about, and you swore some of the eyes on the buildings were staring at you. At a loss, you covered your eyes with your hands, praying that the damn thing wouldn’t drop you. 

A yelp escaped you as you felt something make contact with your body, and you uncovered your eyes only to find that it was a floor. The carpet was patterned with vibrant colors and shapes, and you followed it all the way over to a simple desk resting to your left. Jolting, you got to your feet rather quickly and stumbled in the process, for the man sitting at the desk was none other than the Warden himself.

He had his feet propped up on his desk, and, for some reason, was balancing a pencil between his nose and upper lip. His eyes flicked over to you and he allowed the tool to drop, smiling over at you, “Thank you, Jailbot! I’ll take it from here.” 

The robot, or Jailbot, as you supposed its name was, flew off the way it came, and you stumbled back as the windows leading to the outside slid upwards from the floor and stopped at the ceiling, silencing all outside noise. The only sound in the office was your ragged breaths, a hand moving to your chest as you tried to steady them. At a loss, and utterly confused, you found yourself asking hoarsely, “A-are you going to kill me??”

“Kill you?” the Warden repeated incredulously, followed by a humored laugh, “Oh, that’s silly! Why would you think that? No, I wanted to bring you here because you’re a bit of an enigma, as it were. How on earth did you manage to escape all of that? Here – have a seat.”

You started as a chair emerged from the ground on the other side of his desk, looking plush and comfortable, and you found yourself walking before even fully realizing it to sit down in it, sinking into its soft surface. After two weeks of sleeping on a rock-hard cot, this was a welcome change, even if it was brief. “I really don’t know how; I guess I just have dumb luck…”

“But there _has_ to be more than that,” the man insisted, gloved fingers splayed out over the surface of his desk. “You’re not like the other prisoners; I can tell. You’re not nearly as bloodthirsty, you’re polite, and you’re not revolting to look at!” Was that a compliment? You found you were too distracted by the situation to think on it too much. Warden continued, “These are all qualities that I’d never expect to find so soon in my Superjail. Why were you even convicted?”

You stared over at him, and slowly replied, “Jaywalking. I was arrested for jaywalking, and the prison bus that I was on was kidnapped by your robot, and it dumped me here.” Hastily, you continued, “I-I’m really not a bad guy, War – sir. I was just in the wrong place at the wrong time; I’m not a hardened criminal like the others here…”

His eyes narrowed further, and anxiety had just begun to well in your chest when a smile crossed his lips, which parted to reveal his shining white teeth, a gap between the top two. “See? I was right after all. With someone like you here, you’ll be rehabilitated in no time!”

Somehow, you managed a nervous smile, but his gaze wouldn’t leave you, and once again, you felt yourself growing self-conscious. You were probably supposed to leave, you figured, and you stood to do so, but just as you began to push yourself up, Warden stood as well. “No, no; you don’t have to leave! I enjoy your company; this office gets so quiet. Do you want a drink?”

Confusion crossed your face, though you lowered yourself back down into the chair. Why was he being nice to you solely because you escaped a prison riot without a scratch? Was he just… lonely? Shifting in your seat slightly to adjust yourself, you cautiously replied, “Uh… water? Clean water? That would be nice.”

Warden simply snapped his fingers, and you started as a crystal-clear glass full of water appeared on the desk in front of you. You reached out to take it, wrapping your fingers around the glass and taking a small sip, too thirsty to wonder about how on earth he did that. You found that the more you questioned things in this place, the more it made your head hurt. 

“Let me get rid of that for you,” he spoke, and you had no time to react, for the next time you blinked, the dampness in your jumpsuit was gone. You looked down to find that your clothes were free of bloodstains and smelt as if they were freshly washed. Warden was still smiling over at you when you looked back up, and he asked, chin resting on top of his folded hands, “What’s your name, anyway?” You told him, and he leaned his head further into his hands. “What a nice name… fitting, I think.”

You gave him a patient smile and took another sip of your water. Drumming your fingers along the glass, you said, “Thanks for, uh… not killing me and giving me water. It’s nice.”

He only chuckled – more of a giggle, really – and waved his hand as if swatting away a fly. “Don’t worry about it; a prisoner such as yourself deserves more than that, I’d think.” What was that supposed to mean?

Looking up, you found that Warden was still staring, though when he met your eye, he looked hastily down to his desk and traced a finger over its surface. At his small smile and body language, it all hit you at once. 

This guy had a god damn crush on you.

But why, you wondered? Was it because you were slightly above “human filth” status in comparison to everyone else around there? Did your hair actually look right for once? Christ, you had only met him, what, five minutes ago?

Pondering this, you absently held a hand to your chin. Maybe you could use this to your advantage. If you were in close contact with the Warden and got in his good graces… maybe you could get the hell out of Superjail faster than you thought. “So, Warden,” you spoke, trying to relax your posture a bit, “What – “

You had no time to finish your question, for the chair you were in suddenly turned into a couch, jolting you and causing you to yelp. Warden unceremoniously stood up, stepped over his desk, and turned to fall back onto it, landing on the couch haphazardly and laughing at your shocked expression. “No reason to be so far apart, right?”

Were this a different situation, you would have said that this was actually much more awkward than talking across a desk, but you instead made yourself smile and sat up a bit straighter, “Hey, the couch is comfortable; I can’t blame you.” You took another sip of your drink and continued, “But, as I was saying… what’s it like being the owner of an entire jail? Seems stressful.”

“Oh, I don’t think it is,” he replied, a finger to his cheek. He tapped it against the skin in thought as he spoke, “I have just about everything I need here, and if things go wrong, then I can have it taken care of lickety split! Perks of being the best Warden around.” 

You nodded and hummed in acknowledgement, taking another sip. “And what about your prisoners? They seem pretty rowdy, huh? I mean, they’re criminals, but still. Seems kind of overwhelming to me, especially when they don’t cooperate like you’d want them to.”

Warden gasped, both hands to his face now. “See? You get me! Gosh, I love running a prison, and I love rehabilitating criminals, but it’s so hard when they’re all so stubborn and… and gross.” He folded his arms, seeming to almost pout, and you couldn’t help but smirk a bit to yourself. How uncharacteristic for a prison warden to be so… childish? It was almost sort of charming.

“And that,” you replied, “is totally reasonable. You have every right to be upset by it – who wouldn’t be? You’re just trying to be the best warden you can be, and it shows.” Feeling bold, and silently praying that he wouldn’t flip his shit, you lowered your right hand down and cautiously placed it on his leg, giving it a friendly pat. “You deserve to relax.”

To your surprise, or maybe not, his cheeks almost instantly flushed pink, holding a hand to one and looking to the side. “W-well, I just never have the time anymore… Superjail’s a demanding place to be; I’m almost always busy doing something or other around here.”

“And that’s all the more reason to try and relax,” you urged, taking this as a sign to keep your hand down. You gave his knee a small rub, hoping it wasn’t too bold, and continued, “I could probably help you, if you wanted. I know some stuff that’s helped me in the past when I was stressed and busy.”

You saw Warden visibly swallow, a sheepish smile on his face that he tried to mask with his hand. It was almost cute, and you allowed yourself to let go of the strangeness of the whole situation. If Warden was this easy to win over, you would be out of there in no time. “I… could probably use the help, yes,” he responded, glancing at you from the side, too timid to turn his head. “What do you, ah… usually do?”

Carefully, you sat your water glass down on the desk, taking care to not remove your hand from his leg. You shifted to face him more, still smiling calmly, and answered, “Well, I used to meditate a lot in high school whenever exams were stressing me out. It’s really not that hard; you just kind of…” You moved your hand up by about an inch, “let your body relax… you let go of any of your worries, and just… calm yourself.”

“I could probably try that,” Warden said with a small nod. He took in a deep breath and closed his eyes, leaning back against the couch a bit. Smiling to yourself, you took this as a sign to continue, your tone even and low. “Relax, Warden… focus on your breathing and your senses. Sound, touch, smell… things like that.” You gauged his reaction as your hand moved further up, and his breath lightly caught, though he forced himself to keep his hands at his sides. 

Your palm rested on his thigh now, a smile crossing your lips as you gave it a small, soft squeeze and eliciting a quiet inhale from the man. This was too easy. You had never even done this before, and truth be told, it was a little exciting. Thumb gently rubbing against his hip, you asked quietly, “How are you feeling now? Relaxed?”

Warden swallowed again, chest rising and falling as he took in a deep breath and exhaled. His voice was somewhat meek as he responded with a soft, “Yeah…” and absently flexed his fingers at his sides. You hummed shortly, and, testing your bravery, gently moved your hand to the center of his pelvis. When he didn’t seem to mind, your fingers ever so lightly grazed over his groin, and that movement alone caused a hand to move up from one of his sides. However, it only went to his face, his eyes still closed as he curled his hand around his mouth and let out a small breath.

The lack of shape between his legs left you a touch confused, and experimentally, you instead moved your middle finger down over the expanse of it, your suspicions confirmed. Warden’s breaths were growing a touch more labored now, and you couldn’t help but smile – he was like putty in your hands already, and you were barely even touching him. Would getting in his pants really get you out of there? You found that the thought of escaping was fading further and further into your mind, and the only thing present was the situation you had landed yourself in in that very moment.

When you inched your hand back, you could have sworn you heard Warden softly whimper behind the hand over his mouth, but you only chuckled as your fingers moved over the zipper on his trousers and slid it down. “I’m not going anywhere; just relax…”

Nudging his fly down and briefly taking note of his underwear, which were purple, because of course they were, your fingers teasingly slid over the skin, nudging the hem of his undergarments. They eventually slipped inside, and your hand moved lightly over his groin, fingers barely touching the surface of his labia. 

Warden spoke, voice a bit shaky as he looked to the side, “I’ve… n-never… nobody’s ever- Ah!” You had silenced him by gently rubbing your palm over its surface, middle finger parting his labia and rubbing up against his inner folds. His hand went back over his mouth, eyes still closed as his breaths grew a bit shakier. This was all still so surreal, but damn it, you were going for it.

“Wet already,” you murmured, the base of your finger slipping over his clit and causing his breath to hitch. The digit gently prodded against his entrance, and just as he had inhaled to say something, you slipped it inside and caused the man to finally release a soft moan. He covered his face in both hands, arms lightly shaking as his glasses fogged with his warm breaths.

You let out another small hum, other hand moving over to rub against his thigh as the previous one had. His walls were warm and wet, the man a flustered mess as you gently pushed your finger as far inside as it would go. It began to move in and out at an achingly slow pace, Warden’s face and neck beet red with blush. A warmth was spreading over your own loins, attempting to ignore it as you placed your thumb down on his clit and rubbed at it. You heard Warden murmur your name under his breath amidst his soft pants, legs quivering. 

Your finger brushed against a sensitive spot, for he let out a shaking gasp, and he said your name again, more firmly this time. Your movements halted, and you looked to the man for clarification. Warden’s face was red, looking to the side still and too flustered to make eye contact. Shakily raising a hand, he pushed up his glasses and said quietly, “Please… I n-need… I…”

While you weren’t entirely sure what he meant, you could make enough of an assumption. Your finger slipped out of his core and out from his underwear, hand slick with moisture. Both hands moved to slide his trousers down his hips quite swiftly, leaving him in his underwear and boots, the former now soaked through and damp. Moving over for purchase, you carefully took hold of the man and pulled him over into your lap, causing him to yelp with surprise as he steadied himself. 

Hands resting on Warden’s hips, you shakily smiled up at him, for he was finally making eye contact with you and seemed unable to look away. The man appeared starstruck, taking in your features bit by bit, his blush spreading to his ears. It couldn’t help but make you feel flustered too, but there was work to be done, and with his pelvis pressing up against the tent in your jumpsuit, you were growing impatient. You trailed a hand up his side and rested it on his cheek, earning a soft, flustered gasp, and you spoke breathily, “Give me a hand… would you?”

Warden’s eyes widened behind his fogged-up glasses, and slowly, he looked down to your hips and lowered his hands down, fumbling with the button due to his shaking fingers. He finally unclasped it, pulling it aside and taking the hem of your underwear, only to pull them down too. Your member sprung free from beneath its clothed bonds, you exhaling with relief. The man in your lap seemed almost mesmerized, his gloved fingers moving over the head and gasping quietly when precum slipped over the fabric.

Your hands found their way back to his hips, gently lifting him up – he was a lightweight thing, really – and positioning him just above your cock. A thumb moved out to pull his underwear to the side, exposing his plush, dripping entrance, almost visibly pulsating with need. Warden placed his hands on your shoulders for purchase, biting loosely down on his lip and nudging his hips forward a bit, desperate for what was about to transpire.

You leaned forward a bit just as the head of your member rubbed over his labia, earning a moan, and murmured against his ear, “I never took the Warden for a slut…” just as you began to slip inside of him. Warden made a noise akin to a squeak, the sound dissolving into a sensuous moan. A groan of your own softly passed your own lips, nudging deeper and deeper into his core until his pelvis rested against yours, firmly resting on the base of your cock.

Your arms gently held him around his waist, though a hand moved up to lightly adjust the hat that was already becoming askew atop of his head with a shaking, but warm smile. “If you w-want me,” you spoke, trying your best to maintain your cool, seductive tone, “then you have to work for it…”

Warden’s eyes widened, cheeks burning, and after a shaking gulp and using your shoulders for purchase, he carefully moved up, biting down on his lip and squeaking. He then lowered himself back down and found himself melting against your front as he steadily got into the rhythm of it, moving up and down on your member. His arms snaked around your shoulders, quite literally stretching around you until they curled around your upper torso no less than two times over. His walls were tight and warm and wet, slipping up and down your cock with ease.

A hand found its way to your hair, fingers carding through the strands as Warden panted heavily against your ear. Pleasure was building for both of you, little gasps escaping the man whenever your cock nudged up against the deepest part of his core. His labia was flushed and pulsating against your shaft as it rubbed up and down, his eyes closing as he whimpered softly and buried his face in your shoulder. It caused his hat to go askew, inevitably falling off and rolling across the couch, though neither of you seemed that concerned about it. 

While his head was near, you took the opportunity to tilt yours and press a kiss to his ear, earning a soft, but shrill moan as his hold around you grew tighter. You breathed against it, breath hot, “You like this, Warden…” Gently nipping at his earlobe, you added lowly, “You like being fucked and used like this… we only met this afternoon, and I’m already inside of you…” One of your hands moved down to his rear and gave it a squeeze, eliciting another moan as he bashfully buried his face further into your shoulder. Dragging your tongue over his jawline, you pressed a kiss to it and added, breath catching, “Little whore…”

Warden whimpered, the sound turning into another low moan, bouncing up and down your cock at a steady, faster pace. His moisture was trickling down your length and dampening your jumpsuit, the man nearly dripping even though he was packed tight by your member. A pleasure was building in your gut, holding onto him tightly, and if his shrill, shaking moans were anything to go by, you felt like he was growing close too. 

You waited until you felt his walls clench around your cock, body shaking as he rode out his orgasm, before it became all too much for you, and you came, shoved fully inside of him and flooding his insides with your seed, cock pulsing as you shakily pulled out of him. Warden collapsed against your chest, breathing ragged and his thin form shaking. He still held you tightly with his elongated arms, and you held him close to you in return.

Breaths heavy and hard, you shakily brought a hand to the man’s face, holding his cheek and gently lifting his head up. “Hey…” you breathed, “you… okay? That was… p-pretty intense…”

The Warden replied in the form of a tired, but happy smile, and responded by curling up against you as best as he could, your hand on the small of his back to hold him in place. He murmured quietly, “I think… y-you and I are going to get along just…” He took in a deep breath, then exhaled, closing his eyes fully, “f-fine…”


End file.
